Has there been "prescriptive" attempts at language-learning/comprehension in AI?
Yes.  You're basically looking for "rule based" NLP.  For reference, see:

https://en.wikipedia.org/wiki/Rule-based_system

https://www.quora.com/Why-are-rule-based-methods-becoming-unpopular-in-NLP-Are-rule-based-methods-still-in-use-If-yes-where-should-I-look-for-them

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3756254/

https://nlp.stanford.edu/software/regexner.html

http://u.cs.biu.ac.il/~yogo/courses/sem2014/intro.pdf

etc.